A New Hydrogen-Bonding Motif for Chiral Recognition in the Diastereomeric Salts of Racemic 1-Phenylethylamine Derivatives with Enantiopure O-Ethyl Phenylphosphonothioic Acid

An enantiopure phosphonothioic acid showed a unique and superior chiral recognition ability, arising from its P-stereogenicity, for racemic 1-phenylethylamine derivatives through diastereomeric crystallization. Spherical molecular clusters, associated by hydrogen bonds and CH/π interactions, aggrega...

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Bibliographic Details
Published in:Organic letters 2004-11, Vol.6 (23), p.4227-4230
Main Authors: Kobayashi, Yuka, Morisawa, Fumi, Saigo, Kazuhiko
Format: Article
Language:English
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Summary:An enantiopure phosphonothioic acid showed a unique and superior chiral recognition ability, arising from its P-stereogenicity, for racemic 1-phenylethylamine derivatives through diastereomeric crystallization. Spherical molecular clusters, associated by hydrogen bonds and CH/π interactions, aggregated with high symmetry in the less-soluble diastereomeric salts.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0483145